Planned giving is the most powerful engine of endowment growth, yet most nonprofits lack a structured strategy connecting the two. Transformational bequests — from Annenberg to a Vermont janitor — prove legacy gifts are about trust, not wealth. Strong organizations align development, investment, and governance around long-term sustainability. A 30-question self-assessment helps leaders identify gaps. When those structures are in place, donor confidence follows — and so do the gifts that fund missions for generations.